


The Naughty Professor

by PassionPhantom



Series: Sex on Sundays [1]
Category: Supernatural
Genre: ....full warning, ...Other sex toys, ...Professor Novak (actually), Alternate Universe - College/University, Anal Fingering, Anal Sex, Betrayal, Castiel Has a Large Cock (Supernatural), Cock Rings, Dildos, Don't Ask, Double Anal Penetration, Double Penetration, High Heels, Just read....lol, Lingerie, Loss of Virginity, M/M, Oh I forgot....., Oral Sex, Panty Kink, Plot Twists, Professor Castiel (Supernatural), Rimming, Shit goes down.....watch out y'all., Still this is some sexy stuff., Top Castiel/Bottom Dean Winchester, Twink Dean Winchester, Vibrators
Language: English
Status: Completed
Published: 2019-10-07
Updated: 2019-10-07
Packaged: 2020-11-26 03:22:50
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,637
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20923352
Author URL: https://archiveofourown.org/users/PassionPhantom/pseuds/PassionPhantom
Summary: As soon as Professor Castiel Novak saw the college freshman, Dean Winchester, enter his class, he knew that he was going to fuck him. For Dean, the feeling was mutual.Luckily for the two of them, Dean was failing the class.





	The Naughty Professor

**Author's Note:**

  * For [Andromytta](https://archiveofourown.org/users/Andromytta/gifts).

“Hurry up and bring that beautiful ass over here, Winchester.” Professor Castiel Novak ordered as he laid on the wide hotel bed, wearing nothing but a thick shiny black ring around his massive cock. He was aching, and hard as a diamond from hours of careful edging.

Stepping nervously out of the bathroom, Dean blushed at the sight of the older man. From across the room, he could see the heavy girth and wild length of his professor’s cock. It made him nervous and slightly ashamed, not because of his failing grades, his struggles with keeping up with his classes with work, or because of what he was about to do with his teacher. Dean was ashamed because he’d been secretly wanting to fuck his new professor since the beginning of the semester. 

Wish fulfilled, right?

“You look gorgeous, Mr. Winchester...Don’t be shy.” Professor Novak smiled at his young student. Dean blushed a deep crimson under his freckled cheeks, and felt his thin shoulder’s shake. He didn't know how to carry himself as he was wearing frilly pink and red lingerie with a matching pair of stilettos. 

The young college freshman flinched as he wobbled over carefully, and felt the heat rise in his skin. Dean licked and bit down on his lips, trying to keep his big green eyes averted from studying Professor Novak’s cock any further. The dark-haired man noticed this and chuckled, “It’s okay to look at it. It’s all yours for tonight, anyway.” 

Dean’s eyes shot up immediately and he took an eye full of it. His mouth suddenly watered and he grew hungry to do everything he could ever think of to it. 

“It’s so fucking huge, Professor. I’m not sure if I will be able to take it.” Dean tried to laugh away his nervousness. He climbed onto the silky bed sheets, making sure he poked out his ass with a sweet arch so the man could get a nice view of him in the lingerie. The Professor smirked again.

“Don’t you worry about that part, Dean. I got you.” Professor Novak reached for Dean and guided him closer so he could rest on his lap. Leaning up, Professor Novak slapped Dean hard on his ass and lustfully laughed as he watched the plump freckled skin giggle.

He had been wanting to fuck Dean Winchester for ages, and was purposefully pursuing him throughout the first semester. Professor Novak loved how the young freshman was so willing and eager to be a part of his class. Dean’s big bright green eyes lit up every time he saw Professor Novak. The man had to always kept his composure whenever he taught or lectured the class as he would watch Dean and make sure he was paying attention. Dean paid attention alright. The Professor knew that his student was watching him, studying how thick and muscular his body was. Wondering how big his cock was….Professor Novak knew and made plans to ensure that the freshman would be all his. 

It started with the first essay. Dean’s paper was actually good but the Professor made sure to critique it brutally, giving Dean a D minus. Dean was furious, and even requested another try. That second chance, he received a C minus. The next assignment, another D, and for the rest of the semester, every grade was a D or lower. 

Professor Novak knew that his student would catch on sooner or later. Hell, he knew that Dean was fully aware of his own desires so the deception was totally horrible. Like Professor Novak would care, either way. He bedded dozens of gullible students with this little trick and Dean was nothing special. Besides, the eighteen-year-old looked fantastic in lingerie. 

“So you want to pass my class...Mr. Winchester, are you ready to put in the work for it?” Professor Novak asked.

“Yes, sir.” Dean nodded and continued to writhe around.

“Come on then and suck this dick.” Professor Novak spoke deeply and salaciously as he scooted down to position his body at a decent angle. His cock standing tall and twitching with a mind of his own. Dean’s lips shivered at the sight of it.

_ ‘Am I actually ready?... I have never done this before...not with a guy. A man. Oh my God. I should really tell him this...but I...I want...want’ _Without anymore thinking, Dean leaned forward and took the man’s dick into his mouth. He started slowly...So slowly, until he grew comfortable enough to suck harder and bring Professor Novak’s cock deeper into his mouth.He gagged harshly and heard the man he was sucking on, groan, chuckle, and then groan again.

Professor Novak knew Dean wasn’t going to be skillful at sucking dick, but he was surprised to find that he actually liked it. He enjoyed the feel of Dean’s full pink lips tremble over his tip, and how his throat twitched whenever he tried to deep throat him. 

“Hmmm… tongue the shaft, lick it and make it wet.” The professor ordered his student with a firm tone. Dean’s big green eyes flashed up, innocently, at the man before he moved to lick all around Professor Novack’s girth.

“That’s right, boy.” Professor Novak smiled deviously, “Now, spit on it. It’s not wet enough yet.”

Dean obeyed and started to spit over the cock and then lop up the saliva, tonguing the thick hardened flesh. He tasted the older man and felt the throbbing veins against his tongue. Moaning and wiggling around, young Dean licked and kissed on Professor Novak’s manhood until the older man said, 

“Now spit and suck on my balls. Suck on them hard.” 

Dean angled his face downward and spat heavily, then sucked. He sucked as hard as he could, pulling on the flesh of the professor's thick low-hangers. Without thinking he reached up and touched the man’s hard, muscular body. Feeling every ripple and curve of muscle under his smooth flesh, Dean squirmed a little. He felt himself swelling up and growing hard. It was like a dream damn near come true...he had his Professor’s fat balls in his mouth. It was all he ever wanted. 

Dean hummed and pulled back on the older man’s left nut. Slurping on it and popping off of it before moving to do the same to the right side. He could hear Professor Novak’s moans, chuckles, and his _ ‘good boy’s’ _as Dean worked all around the man’s groin. 

“Alright, open wide.” Professor Novak ordered and Dean complied. His eyes widening as his instructor slowly inched his cock into his mouth. Dean gagged and squirmed but allowed the man to push upward until he was in the back of his throat. Dean moaned and his eyes watered while his body tensed up. 

“Breathe through your nose, boy.” Professor Novak said and pushed down on the back of Dean’s head, refusing to let him come back up. The student was going to be in for one hell of a lesson, tonight. Professor Novak was going to make sure of it. 

Dean struggled for a moment...he did have an entire cock inside his throat so he attempted to breathe as directed. The air rushed through his nostrils and it was a relief. 

“Keep breathing,” He heard the older man say. Dean obeyed and continued until he felt his throat loosen up and his eyes become less watery. Dean groaned and patted Professor Novak's thighs, letting him know that he was ready to perform correctly this time. The Professor loosened his grip on Dean’s hair and massaged his scalp, making Dean moan in pleasure. His head began to bob slowly.

“That’s it...that’s it, right there...just like that. Just like that.” Professor Novak moaned and growled in satisfaction while continuously running his hands against Dean’s tight lithe body.

Dean sucked hard and started to really enjoy himself as he got more creative. He tongued the shaft while deep throating correctly, and was allowed to pull up to not only breathe, but to tongue the man’s tip. Teasing the slit, Dean tasted his instructor’s pre-cum, making his eyes roll back, as he relished in the sweet but musky taste. It felt so good, and listening to the man actually enjoy himself made Dean’s dick even harder. 

Then Professor Novak pulled Dean up off his cock and gripped his hair. Dean complied with the sudden movement and allowed his professor to kiss his full wet lips. They both groaned as their lips smacked, as they tasted one another. Grazing their tongues together and allowing the silky warmth to make them both shiver. Professor Novak eventually chuckled at the feel of it and said, 

“Don’t make me come yet, Sweetheart, I’m wearing this cock ring for a reason.”

“I want you to fuck me now,” Dean said anxiously and his teacher laughed. 

“Not yet, we still have plenty of work to do, Mr. Winchester.” 

Dean watched as his professor slowly flipped him around until Dean was lying on his stomach. Hoisting up the student’s hips, Professor Novak slid down while positioning his face near the younger man’s beautifully plump ass. Professor Novak salaciously sucked back on his teeth. Dean was such a gorgeous sight to see in these frilly panties and stockings. The man smiled enjoying the view and running his hands down Dean’s freckled legs to his ankles. From there the older man lightly touched the smooth stilettos, caressing the arch of Dean’s feet. He admired the look. Most of his other students had never looked so good in the lingerie, but Dean...Dean was something else. Something lovely. The thought made Professor Novak’s cock twitch and he slowed himself down…

_ ‘Hold on Castiel...hold on.’ _He thought, biting down on his lip and watched as Dean’s cute ass quivered while he caressed the cheeks. “Oh, Dean, you are so fucking beautiful...just breathtaking.” 

“Well, thank you, Cas.” Dean said playfully, earning him a swift rough slap on his backside. 

“It’s Professor Novak, to you boy.” Professor Novak chuckled watching Dean’s ass cheeks turn red and quiver. Dean moaned and wiggled a little. He actually liked it when his professor played with his ass and the anticipation was killing him. He wanted desperately to be fucked...he wanted to know what it was going to feel like; to have a man inside him. A man who was so large.

“Please, Cas,” Dean said and earned another slap. The young man grunted and repeated his instructor’s first name, writhing as he received more strikes. He moaned and felt his own cock throbbing uncontrollably. It felt so good, his professor spanking his ass made his cock grow harder with each smack. 

“Okay, Professor! Okay!” Dean squealed out and laughed for the last time and flinched as Professor Novak still applied another hand to his blushing red cheeks.

“You’re going to be a good boy, now?” Professor Novak asked grinning. Dean looked back and smiled wide, 

“I’ll be the best boy.”

Professor Novak chuckled, “I’m going to make sure of that, Dean Winchester. I’ll make sure of that.” 

Turning his attention back to his student’s backside, Professor Novak, tucked his fingers under Dean’s panties and pulled them off. Throwing the frilly underwear over his shoulder, Professor Novak moved to open Dean up and saw the bright pink muscle. Professor Novak’s eyes widened and his mouth watered as the realization hit him...Dean’s hole had never been fucked in before. 

“Oh shit,” Professor Novak gasped and grinned devilishly as if he was in for a real treat. Not only was his student, young and attractive, but practically a virgin, who was willing to suck his cock and get fucked. Professor Novak licked his lips as his mouth watered; he was indeed about to enjoy himself. Dean was like a Christmas gift...just waiting to be opened up. 

“Professor Novak...I’m waiting---Aw!” Dean had started but suddenly moaned as he felt the man’s wet tongue smooth over his hole. His body shot up the bed and he squirmed as his professor started to lick, kiss and suck on his ass. 

“Ah, fucking shit!” Dean gasped and started to sweat heavily. Professor Novak’s tongue was firm, strong, and he licked Dean’s muscle in a steady circular motion. Dean squirmed away as his tight hole became wetter and loose from the constant attention. 

“Don’t you go anywhere…” Professor Novak ordered, as he pulled Dean back and dug his tongue deeper into him. Slicking it over the hole and feeling it pucker, wildly. 

“Ooooh, fuck. Come on Teach’, just fuck me already. I can’t take it---OH FUCK!!!” Dean begged then suddenly roared. Professor Novak--without warning--shoved his middle finger into Dean’s entrance and went straight for the eighteen-year-old’s untouched prostate. The student’s reaction was pure gold and Professor Novak bit back a laugh. He focused on fingering the young man’s hole, thrusting his finger and teasing the prostate. He rubbed relentlessly against Dean’s sweet spot, stroking it, flicking it and teasing him. All the while watching Dean lose his fucking mind. 

Dean thrashed everywhere on the king-sized bed. Squealing and trying to escape the constant stimulation, he kicked his legs, moved his hips, knocked over pillows and gripped the sheets for purchase. He screamed, gasped and shouted. His ass cheeks clenched up around, Professor Novak's finger and his toes went numb. Professor new the feeling too well when an ass contracted like such...he knew when he was about to make a student come. 

“Don’t you fucking dare!” He shouted his demand and grabbed Dean’s hips up. Dean moaned out and shook as the older and skillful man reached under and gripped his balls and tugged on them. “Don’t you dare come before I say you can, Boy. You bust that fucking nut and you’ll be in a world of trouble.” 

“Yes-s, sir...I won’t. I won’t. I promise!” Dean shuddered and felt his body unclench and relax. Professor Novak released him and let the younger man fall back down to the bed. Allowing him to rest for a moment, the professor took his cock and slapped it against Dean’s ass. 

“Ugh, please...please, Professor! Please!” 

“Shhh.” The professor said before spreading Dean’s ass open and hocked back. He spat heavily onto his cock and then a couple more times in Dean’s hole. His fucking cock was throbbing now painfully. It was mind-numbing and the attractive middle-aged man was so ready to fuck Dean’s pert ass. 

Starting off slow, he inched his way in and growled feeling Dean react. He was wickedly tight and Professor Novak struggled a bit to get inside. Groaning he inched in further. Holding firmly on Dean’s writhing hips. Listening to the high pitched guttural sounds Dean Winchester made as he got filled up with a cock for the first time ever in his life. 

“Damn, you’re so tight.” Professor Novak grunted as he pushed in deeper and deeper. Before he knew it he was completely sheathed inside of Dean and he pulled out slowly to only hear the sounds Dean made once more. To feel his body ache around his cock...then he slammed his hips. Dean squealed out and from there the man went wild. 

Pounding and pumping savagely into the young freshman, Professor Novak grunted, shouted and roared. Sweat dripped down his face as he labored intensely. Fucking at a vicious and murderous speed. Enjoying the squeals, moans, and shrieks escaping Dean’s throat, he pulled on the student’s sandy brown hair and fucked him non-stop in thick violent strokes. Thrusting so hard that the room was filled with the sound of wet skin slapping together. The Professor enjoyed the sound far too much and started to pump upward while still pulling on Dean’s hair. Making them fuck at a delicious angle which provided a louder smack as Dean’s fat backside clapped against the Professor’s groin. 

“Ahh! Ah! AW!” Dean let out just as his instructor teased--

“Clap those fucking cheeks, boy.” The man laughed and continue to thrust and Dean mindlessly obeyed. Throwing his hips back and listening to the sound increase. The seconds passed into minutes, the two fucked into each other so hard that Dean’s ass became a raw bruised red. His eyes were rolled to the back of his head in ecstasy and his hole was growing looser from each pound his professor delivered. 

But again, before Dean could bust his load, Professor Novak pulled out. 

“Ahh, Shit! Come on Teach’!” Dean begged and looked back as the man walked over to his briefcase and grabbed some of his _ tools. _Dean’s eyes widened as he saw Professor Novak return to the bed with a black veiny dildo, vibrator, and a clear large fleshlight. 

“HOLY FUCKING SHIT!” Dean bellowed. He didn’t even know it when the man flipped over on his side and climbed up behind him. What he did know was that his instructor was suddenly fucking him brutally with both his cock and the dildo at the time. 

“Don’t run from it...Stop running boy! Stop running! Take it! Just take it!” Professor Novak ordered and double fucked the shit out of his student. Fisting the dildo into Dean’s raw ass, and rutting him like a wild animal. Dean was enthralled and couldn’t believe his first time with a guy...a grown-ass man, would double penetrate his asshole without any help. 

“Ahh! Goddamnit, CAS!” Dean shouted and bit down on the sheets. His brain was on fire and the world was turning into itself and Dean swore he was about to come. It was like the man could read his mind, Professor Novak slammed his cock in...hard, ripped out the dildo, and pushed the object into Dean’s mouth. 

“Suck it.” Professor Novak said and Dean complied---he was so turned on and confused all at once. Dean sucked on the onyx colored dildo as hard as he could while his professor took the vibrator he had from before and applied deep into Dean. 

He turned it on. 

“M-HMMMM!!!!” Dean moans were muffled and he froze hard as the insides got vibrated, buzzed and fucked in all at once. Professor Novak laughed and relished as he felt the vibrator send ripples of pleasure all over his cock while inside of Dean. 

“AH Fuck YES!!” The man started to rut again and even he started to thrash around the bed with his student ...his whore for the night. Grabbing hold of the vibrator and keeping it inside Dean, Professor Novak crawled around Dean and fucked him in the missionary position. Sharing the wicked vibration the two kissed and took turns sucking on the dildo.

The hotel room was filled with the filthiest noises and the two of them enjoyed the craziness of it a bit too much. The people next door could even hear it and they heard their serious complaints. The professor and the student didn’t care. The fucking continued, Professor Novak continuously pulled out and fucked Dean in multiple positions while demanding him not to come. 

Not until he applied the large fleshlight to Dean’s cock. Pumping the sex toy and fucking the younger man’s hole, Professor Novak heard Dean begging, 

“Can I come now?! Can I come now?!” Professor Novak pushed his dick up in Dean hard and pushed the fleshlight downward, holding everything still as he whispered, 

“It’s ‘May I,’ boy...say may I?”

“Are you serious--?” Dean groaned and received a smack on the ass. He flinched, 

“May I!” He shrieked and Professor Novak started to fuck him again. 

“May you what?” The man growled and jerked the fleshlight on Dean’s cock. Dean was so overwhelmed that he started to cry. This alarmed Professor Novak and he kissed Dean’s cheek to soothe him. “May you what?” 

“May I come now...May I come now,” Dean whimpered and Professor Novak smiled devilishly and started to speak to Dean in between pumps,

“Yes. You. MAY!” Professor Cas Novak shout thunderously and in that instant, Dean shot a heavy load into the fleshlight and he wailed out with no control over his mind or body. He came so hard that the eruption made his chest heave, his stomach cave in and his eyes see stars. Dean didn’t hear his instructor coming alongside him. 

Screaming and bellowing out, as he thrust through his orgasm until the thick cum seeped out of Dean’s hole and coated his cock. Even then...he continued rutting, groaning and ravaging Dean. 

The erotic actions continued on through the night until the professor and his student collapsed in exhaustion. 

**Two Weeks Later: **

(Before Christmas break.)

Dean stepped into his dorm room. Finals were wrapping up and all the students at the college were getting ready for Christmas vacation. Dean was relaxed and glad to have a break from school. He hung out with his friends, Benny and Charlie. He partied hard without a care in the world, no longer worrying about his grades. Knowing he made an easy A plus from _ working _so hard with Professor Novak. 

Packed up and ready to go back home to Kansas, Dean smiled as he felt his phone vibrate with a new email. Hell, the vibration almost reminded him of that night with the Professor. Dean laughed and thought,

_ ‘That was one hell of a night...shit. I might as well look at my scores.’ _Dean grabbed his phone and unlocked it. Opening the email and checking his grades and current G.P.A. 

The smile on his face fell. The A he was promised and looked forward to, was not an A-plus ...but an F minus.

Just then a text message notification popped up on his screen over the email. It was from Professor Castiel Novak: 

_ *See you next semester, Mr. Winchester…* _

**Author's Note:**

> A quick bday present to my FB/discord buddy, Andromytta. <3 I hope you like it!
> 
> S/O to my beta, Sidebottom, :D Thanks for handling all my horrible grammar usage. I hope this fic is spicy (lol) enough for everyone and that you guys enjoy it!
> 
> (By the way, I am fully aware that there is the Eddie Murphy movie called The Nutty Professor.....lol this ain't like that. So don't get the titles confused. Haha!)


End file.
